Ammonium Chloride → 1-(Quinolin-6-yl)ethan-1-one

HRID 16023

Reaction equation

HRID 16023 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)=[O:5].[CH3:17][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[N:12]1[C:13]2[C:8](=[CH:7][C:6]([C:4](=[O:5])[CH3:17])=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 55211172N-Methoxy-N-methylquinoline-6-carboxamideHCID 178418689HCID 178418689, compound

Product 1

HCID 2585591-(Quinolin-6-yl)ethan-1-oneYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of quinoline-6-carboxylic acid methoxy-methyl-amide (11.97 g, 55.35 mmol) in anhydrous THF (200 mL) was added MeMgBr (1.5 M in THF, 55 mL, 83 mmol) at 0° C. under nitrogen. The reaction was allowed to warm to ambient temperature over 16 hours. Sat. NH4Cl (20 mL) was added to quench the reaction. The reaction solution was then extracted with EtOAc (3×50 mL). The combined organics were dried over Na2SO4, filtered, and concentrated to give 1-quinolin-6-yl-ethanone (9.2 g, 97% yield).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe reaction solution was then extracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b533ba8a3a34f338769c7d82baef3e5
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Linked notes

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